Potassium Carbonate → HCID 18916435, compound

HRID 1290627Notes

Reaction equation

HRID 1290627 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([N:14]3[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]3=[O:25])=[C:12]([F:26])[CH:11]=[C:10]([Cl:27])[C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH2:34]OS(C1C(C)=CC(C)=CC=1C)(=O)=O.[Cl-].[NH4+]>O1CCCC1>[C:1]([C:5]1[O:6][C:7]2[C:13]([N:14]3[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[N:16]([NH2:34])[C:15]3=[O:25])=[C:12]([F:26])[CH:11]=[C:10]([Cl:27])[C:8]=2[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 18916403HCID 18916403, compound

Product 1

HCID 18916435HCID 18916435, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a stirred solution of 1.0 gram (2.5 mmole) of 3-(2-t-butyl-4-chloro-6-fluorobenzoxazol-7-yl)-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione (prepared in Example 1, Steps A-E), 0.41 gram (3.0 mmole) of potassium carbonate, and 50 mL of tetrahydrofuran was cooled in an ice bath. To this was added 1.1 grams (about 5 mmole) of 1-aminooxysulfonyl-2,4,6-trimethylbenzene. Upon completion of the addition the reaction mixture was stirred in the ice bath for ten minutes, then warmed to ambient temperature, where it stirred for an additional 18 hours. After this time the reaction mixture was poured into 150 mL of aqueous 10% ammonium chloride solution and extracted with two 75 mL portions of diethyl ether. The combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to an oil, which was subjected to column chromatography on silica gel. Elution was accomplished with 6:1 heptane:ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.75 gram of 3-(2-t-butyl-4-chloro-6-fluorobenzoxazol-7-yl)-1-amino-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione, m.p. 90°-92° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. extractionextracted with two 75 mL portions of diethyl ether
  3. washThe combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to an oil, which
  7. washElution
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e34a21a4906340f7bbdc539c39beede0
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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